Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Tert-butyl 4-(4-chloro-1H-pyrazolo[3,4-D]pyrimidin-1-YL)piperidine-1-carboxylate | HCID 57964905 | — |
| Reactant | Quinolin-5-ol | HCID 135441757 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 57965041 | HCID 57965041 | 47% |
Reaction Steps
A mixture of quinolin-5-ol (Aldrich Chemical Company, Inc., Milwaukee, Wis., USA 26 mg, 0.178 mmol), 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tertbutyl ester (Intermediate 19; 60 mg, 0.178 mmol), and potassium carbonate (54 mg, 0.391 mmol) in dimethylformamide (1 mL) was heated in a microwave oven at 160° C. for 10 min. Saturated sodium carbonate solution was added to the reaction mixture, and the mixture was then filtered through a pad of silica gel to remove the precipitate. The silica gel pad was washed with methanol and the solvents were evaporated from the filtrate. The residue was purified by HPLC to afford 4-[4-(quinolin-5-yloxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (37 mg, 47%) as a white solid. Mass spectrum MH+=447.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08188098B2 |
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| Source dataset | uspto-grants-2012_05 |
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| ORD ID | ord-af5871dbeff34117b45777ad483836c1 |
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| Source note | uspto-grants-2012_05 |
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